N-{4-[(3,4-Dimethyl­phen­yl)(eth­yl)sulfamo­yl]phen­yl}-N-ethyl­acetamide

Peter John; Saima Khizar; Islam Ullah Khan; Shahzad Sharif; Edward R T Tiekink

doi:10.1107/S1600536810045708

. 2010 Nov 13;66(Pt 12):o3152. doi: 10.1107/S1600536810045708

N-{4-[(3,4-Dimethylphenyl)(ethyl)sulfamoyl]phenyl}-N-ethylacetamide

Peter John ^a, Saima Khizar ^a, Islam Ullah Khan ^a,^‡, Shahzad Sharif ^a, Edward R T Tiekink ^b,^*

PMCID: PMC3011401 PMID: 21589450

Abstract

When viewed down the central S⋯N axis of the title compound, C₂₀H₂₆N₂O₃S, it is apparent that the molecule adopts a gauche conformation with all O atoms lying to one side of the central benzene ring; the carbonyl O atom is directed away from the central ring and the N-bound ethyl groups lie to one side of the molecule. Supramolecular helical chains aligned along the b axis and sustained by C—H⋯O contacts feature in the crystal packing. These are consolidated in the three-dimensional structure by C—H⋯π interactions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2010 ▶); Khan et al. (2010 ▶).

Experimental

Crystal data

C₂₀H₂₆N₂O₃S
M _r = 374.51
Monoclinic,
a = 8.0882 (2) Å
b = 11.5978 (3) Å
c = 21.2717 (5) Å
β = 97.194 (1)°
V = 1979.69 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.28 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.692, T _max = 0.895
16612 measured reflections
4079 independent reflections
3325 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.122
S = 1.01
4079 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045708/hg2743sup1.cif

e-66-o3152-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045708/hg2743Isup2.hkl

e-66-o3152-Isup2.hkl^{(195.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.54	3.455 (2)	170
C10—H10a⋯Cg1ⁱⁱ	0.96	2.93	3.728 (2)	142

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

In connection with on-going structural studies of sulfonamides (Sharif et al., 2010; Khan et al., 2010), of interest owing to their biological properties (Korolkovas, 1988; Mandell & Sande, 1992), the title compound, (I), was investigated.

With reference to the central benzene ring in (I), Fig. 1, the S1 [deviation = -0.068 (1) Å] and N2 [-0.005 (1) Å] atoms are co-planar. Both sulfonamide-O atoms lie to the same side of the plane as does the carbonyl-O atom, which is directed away from the ring, with the remaining substituents lying to the other side. When viewed down the S1···N2 vector, both N-bound ethyl groups lie to the same side of the molecule. Similarly, when viewed down the S1···N2 vector, the molecule has a gauche conformation.

In the crystal packing, molecules are connected into a helical supramolecular chain along the b axis via C—H···O contacts occurring between benzene-H and sulfonamide-O atoms, Table 1 and Fig. 2. The chains are consolidated in the crystal packing by C—H···π interactions, Table 1 and Fig. 3.

Experimental

A mixture of N-{4-[(3,4-dimethylphenyl)sulfamoyl]phenyl}acetamide 100 mg (0.314 mmol) and sodium hydride 85 mg (0.78 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min. followed by addition of ethyl iodide 199 µl (0.785 mmol). Stirring was continued for a further 3 h and the contents were poured over crushed ice. The precipitate that formed was isolated, washed and crystallized from methanol solution by slow evaporation; M.pt. 472 K.